Physico-chemical Analysis of 3, 3, 5-Trimethylcyclohexyl DL-Mandelate

Abstract

The diastereomeric isomer ratio of 3, 3, 5-trimethylcyclohexyl DL-mandelate (cyclandelate) was examined by various physico-chemical methods. Capillary gas chromatography and ¹³C nuclear magnetic resonance spectroscopy showed that the bulk of cyclandelate which had been determined by proton magnetic resonance to have an isomer ratio of 73 : 27 was actually a mixture of nearly equal amounts of the two isomers. The reason for the difference in the results was studied in detail by an analysis of the physical properties of solid solutions of the isomers.